Hydrochloric Acid → (1R,2S,3R,5S)-3-(4-amino-7-fluoro-3a,7a-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)-5-methylcyclopentane-1,2-diol

HRID 470190Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 470190
[F:1][C:2]1[C:3]2[N:11]([C@H:12]3[C@H:19]4[C@H:15]([O:16]C(C)(C)[O:18]4)[C@@H:14]([CH3:22])[CH2:13]3)[CH:10]=[N:9][C:4]=2[C:5]([NH2:8])=[N:6][CH:7]=1.Cl>CO>[NH2:8][C:5]1[CH:4]2[N:9]=[CH:10][N:11]([C@@H:12]3[CH2:13][C@H:14]([CH3:22])[C@@H:15]([OH:16])[C@H:19]3[OH:18])[CH:3]2[C:2]([F:1])=[CH:7][N:6]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 672505457-fluoro-1-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-1H-imidazo[4,5-c]pyridin-4-amine

Produkt 1

HCID 58329284(1R,2S,3R,5S)-3-(4-amino-7-fluoro-3a,7a-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)-5-methylcyclopentane-1,2-diol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

7-fluoro-1-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-1H-imidazo[4,5-c]pyridin-4-amine (6-5) was dissolved in MeOH (1 mL) and concentrated HCl (200 uL) was added. After disappearance of the starting material, the mixture was concentrated to afford (1R,2S,3R,5S)-3-(4-amino-7-fluoro-3a,7a-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)-5-methylcyclopentane-1,2-diol (6-7) as a brown solid. 1H NMR (500 MHz, CD3OD): δ 8.54 (s, 1H); 7.77 (d, J=5.6 Hz, 1H); 4.95 (q, J=8.5 Hz, 1H); 4.33 (t, J=6.5 Hz, 1H); 3.76 (t, J=6.0 Hz, 1H); 2.54 (m, 1H); 2.11 (m, 1H); 1.60 (q, J=11.0 Hz, 1H); 1.21 (d, J=7.5 Hz, 3H). LRMS m/z (M+H) 267.0 found, 267.1 required.

Aufarbeitung

  1. concentrationAfter disappearance of the starting material, the mixture was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-ab5833f1e1de4da8863043a0784eaed9
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629275B2

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